Dimethyl Sulfide → HCID 57640341, compound

Participants

Reaction Steps

To a solution of N-(2-methylpropyl)-N-[(2,5-dichlorothiophen-3-yl)-carbonyl]piperidin-4-amine (0.72 g, 2.14 mmol) in anhydrous tetrahydrofuran (5 ml) is added BF3.Et2O (0.73 g, 5.14 mmol) and the reaction mixture is heated to reflux. While refluxing, BH3.Me2S (1.6 ml, 3.2 mmol) is added and the reaction vented to remove Me2S for 10 minutes. After an additional 2 hrs at reflux, TMEDA (0.75 g, 6.42 mmol) is added and the reaction mixture heated at reflux for 1 hr. The reaction mixture is cooled, and the precipitate is filtered and washed with dichloromethane. The filtrate is concentrated in vacuo. Aliquots of methanol (5 ml) are added to the residue and concentrated. This process is repeated until no more gas evolution is observed. The resulting residue is purified on silica gel (0-100%) 5% 2N NH3 in methanol in dichloromethane to give N-(2-methylpropyl)-N-[(2,5-dichlorothien-3-yl)methyl]piperidin-4-amine (0.19 g, 28%). m/z=321 (M+1); 1H NMR (CD3OD): δ=6.87 (1H, s), 3.65 (2H, s), 3.34-3.30 (2H, m), 2.86-2.78 (2H, m), 2.74-2.63 (1H, m), 2.26 (2H, d), 1.95-1.89 (2H, m), 1.72-1.58 (4H, m), 0.86 (6H, d).

Provenance & Evidence